


What Happens When You're Pretty

by bluedemon92



Category: Naruto
Genre: Brothels, Crossdressing, Itachi Is Pretty, M/M
Language: English
Status: Completed
Published: 2015-09-24
Updated: 2015-09-24
Packaged: 2018-04-23 04:13:38
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,490
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4862711
Author URL: https://archiveofourown.org/users/bluedemon92/pseuds/bluedemon92
Summary: <blockquote class="userstuff">
              <p>When Itachi is sent to a brothel for information. He certainly did not expect to see Kakashi there.  Or...his brother.  Of course he had to be in a dress for this.</p>
            </blockquote>





	What Happens When You're Pretty

**Author's Note:**

> I don't own Naruto.

Itachi had nice legs. This had been agreed on by the Akatsuki without a doubt. He also had a pretty face. Also no doubt. Nice legs and a pretty face could come in handy in the Akatsuki's line of work. As it turned out... there was information. Key information that Pein needed. The information was in the possession of a wealthy benefactor who often visited local brothels. The man had a soft spot for pretty boys and girls. He often took a young man he deemed attractive to his rooms for the night. It happened that Itachi was exactly his type. Leggy and slender with lovely eyes and long lashes. It was suppose to be an easy target. It was suppose to be an easy mission. It certainly started out that way.

Konan had dressed Itachi in a dark blue kimono with a black obi and a silvery design running down the side. She had fixed his hair up with Deidara's help. Deidara smirking all the while.

"Aren't you pretty Itachi-chan." He had sneered, roughly tightening the sash around itachi's waist while Konan hissed at him to be careful. She placed a flower into his hair and pulled out her makeup tray. She studied him for several minutes.

"I want to accentuate those eyes of yours, without making it too obnoxious." She stated as she lightly began to apply the makeup. "You have amazing skin." She stroked a thumb down Itachi's cheek with an absent smile. Deidara stood close by glaring daggers at the Uchiha. Konan finished up his makeup and helped him to his feet, calling out to Kisame to come in. Kisame entered the room, offering Itachi a toothy grin.

"My, my Itachi. Aren't you a sight for sore eyes." Kisame himself, was dressed in simple garb, forgoing his usual uniform. Samehada however was attached faithfully to his back.

"It's a little short." Itachi stated, sullenly fidgeting with the material. It only came down to a bit above his knees. Long enough to cover everything, but short enough to show off those legs and thighs. Konan laughed, fixing the kimono.

"You're going to a brothel, dear. You need to look the part." She did a final glance over before nodding. "Good luck kid. You'll need it."

"I think he looks good." Kisame said with a shrug and Konan nodded in agreement.

"That's the problem. He'll be getting quite a bit of attention."

"Do I have to fuck him?" Itachi finally asked, looking despondent. Konan pursed her lips unhappily. Whether at Itachi's language or at the answer no one knew.

"If it becomes necessary to get information yes. Pein also wants me to remind you no killing him. You can drug him, but he needs to be left alive."

"Or course."

* * *

Konan, of course was right. As soon as Kisame escorted Itachi into the brothel, several pairs of eyes landed on him. The Uchiha had done a wonderful job of smiling prettily and avoiding the crowds. He stood at Kisame's side until the elder nin wandered off to get a drink, muttering in Itachi's ear to keep an eye out. It did not take long however. Itachi was certainly this man's type. His target had approached Itachi first, eyes alight with desire. He smiled and swept Itachi's hand into his own pressing a wet kiss against his skin.

"It must be my lucky day." He greeted and began to drone on. Itachi his his disgust well and managed a small shy smile, batting his lashes. The target was a large man with a thin mustache and small watery eyes. Itachi managed to nod at the man, tilting his head to the side to show off the long contour of his throat. The target's eyes landed on Itachi's throat, just as expected.

"Should we take this somewhere more...private?" Itachi questioned softly.

The benefactor let out a bark of laughter.

" _You_ my boy have read my mind. Follow me." He guided Itachi towards the stairs and Itachi cast a quick glance at Kisame who showed him a thumbs up and a grin. Itachi scowled slightly before turning back and following the man up the stairs, Kisame grinning all the while.

The brothel was packed. As usual at this time of night. Women and men alike, wandering around and disappearing into different rooms. Kisame accepted the drink offered to him and relaxed against the chair. Every so often his eyes would wander back up the stairs. A woman approached him at one point, her makeup askew and offered him a sly grin which he returned. If he didn't have a job tonight he would have certainly taken her to bed. Instead he watched as she approached a different nin.

"Remind me why we're here again?" An annoyed young voice could be heard behind Kisame.

"You kids need to live a little!" Another voice blurt out smugly.

"You're a pervert!" Another young voice called out in annoyance. Kisame did not turn and continued to drink.

"Now now kids. Don't be testy. We're only stopping by" A voice belonging to a man lazily drawled. He heard another man chuckle and respond. Kisame went to take another swig when he stopped.

He knew that voice.

Bowl hair cut. Thick brows and an awful green jumpsuit. It couldn't be... slowly Kisame turned.

No.

No, no, no, no no, NOOOOOO

There stood Itachi's cranky younger brother and his team. The Kyuubi boy and Kakashi- who Kisame was convinced Itachi had boned. The white haired pervert ninja was among them along with...Might Guy. The old pervert was quick to separate from the group and head towards a busty brunette. No one had noticed Kisame yet... His eyes darted to the stairs, willing for Itachi to hurry the fuck up. Kakashi wandered off as well, Guy following close behind while Kisame fought down a scowl. Why hadn't he disguised himself better!? He was fucking blue! The two boys stood awkwardly at the door, shifting uncomfortably. That made three of them...

He did not notice as Itachi appeared at the stairs, hair out of its bun and fanning around his face, he carefully took to the stairs, grimacing at the movement. He had taken off his heels and held them in one hand. Sometimes fucking the target was necessary. It never made it easier though. Yet Itachi had the information needed. The benefactor would be out for several more minutes, giving Itachi and Kisame just enough time to slip away.

"Hey good looking." A voice drawl and Itachi looked up in time to come face to face with _Jiraiya._

_Shit._

Itachi forced down his panic and offered the pervert a coy smile which was returned. He looked Itachi up and down, smiling appreciatively. He leaned against the banister, his grin widening.

"How about I order us some drinks and we get better acquainted."

Itachi forced a girlish giggle and peered at Jiraiya through his lashes nodding. Grinning the old pervert turned to the nearest serving lady and with his back turned Itachi darted towards where Kisame sat rigidly. However, luck was not on Itachi's side and he was once again caught off guard by Kakashi himself stepping in front of him, smirking cheerily.

"Hey." He greeted and Itachi fought down the urge to giggle madly at his voice.

_Childhood crushes..._

Instead Itachi offered the man a small smile, tilting his chin while praying to whoever was listening that Kakashi would not recognize him. Kakashi regarded Itachi with that normal confident swagger that left Itachi weak kneed.

"You look really familiar. Have we met?"

Itachi shook his head, eyes lowered. Kakashi made a noise of confusion as he studied the...woman? Man? Who cares...

"Do you work here?" He asked and Itachi gave a slight nod. Kakashi smiled again, eyes closing.

As it turned out, as Kakashi spoke to Itachi he would take a step forward and Itachi would back up. This finally occurred to the Uchiha when he realized he and the nin were halfway up the stairs and Kisame had spotted him and began waving frantically, eyes huge. Behind Kisame, Itachi spotted a familiar sullen boy and felt the floor drop from under him.

Shit.

Kakashi had noticed Itachi's wide eyed gaze and began to turn. In desperation, Itachi grasped onto the side of the nin's face and pulled him close,locking his lips against the elder nin's and kissing him deeply. Kakashi returned to kiss, hand grasping Itachi's waist and pulling him close.

That is where everything went to shit.

Kisame's waving arm movements had stilled as he stared slack jawed at the kissing couple. His movement caught the attention of Guy and Jiraiya who instantly recognized and called out. Both Naruto and Sasuke turned to the source of noise eyes widening as they too realized it was Kisame. Sasuke put two and two together quickly and realized Itachi had to be here! Guy and Jiraiya moved towards Kisame who in desperation called out Itachi's name. At the mention of Itachi's name, Sasuke snarled calling out for him to show himself. Sasuke looked around, teeth bared just as Itachi pulled from the kiss, eyes half lidded and widening when he realized they had been caught. He glanced at Sasuke who stared up at him, glanced towards Guy and Jiraiya who were staring at Itachi in shock, eyes huge. Itachi let out a soft groan and shook his head, rolling his eyes. He tossed his heels to Kisame who caught them with one hand. Quickly ducking away from the two leaf nin and shouting for Itachi to run. Behind him, Itachi heard the benefactor angrily an groggily shout that he had been robbed. He stumbled from the room, pointing at Itachi who was still in the arms of a slack jawed Kakashi as Sasuke began to charge at him. Itachi turned back to Kakashi once more and shrugging quickly pulled the man in for a final kiss, halting all action. Sasuke stood at the bottom of the stairs slacked jawed. Staring at his brother in drag kissing his teacher. Itachi pulled back from the kiss offered Kakashi a sly grin and pat his cheek before throwing himself over the banister. He handed cat like on the table below. The benefactor screaming all the while to stop that boy!

Sasuke screamed out to Itachi who shot him an annoyed glare as if to tell him not now! He easily evaded Jiraiya and Guy, fighting off a grin as he raced towards Kisame. Mortifying at the situation was...this was a rush Itachi had not felt in awhile! Sasuke launched himself at Itachi who spun around flicking his brother in the forhead.

"I'm busy "Otouto!" He snapped casting a stern glare of his enraged sibling. Sasuke lunged for Itachi again as the benefactor shouted.

"You whore! You seduced and drugged me!" He screamed and Sasuke's mouth dropped again. At the insult thrown, Kisame had slowly turned to the benefactor, Samehaha lifted and his beady eyes narrowed. The room seemed to drop temperature by several degrees and everyone could feel it.

"Would you mind repeating that comment?" Kisame aked, voice low. Itachi stood near his partner, brows furrowed The benefactor backed away, hands lifted defensively.

"I-I didn't-" He began rambling. Kisame stepped closer, weapon raised. Guy began to slowly try to move between the two while Itachi pinched the bridge of his nose.

"I don't like ugly old men calling my partner names. There are quite a list of ugly old men who have yet to die for their comments. You however..."

"Kill him and we don't get paid." Itachi pointed out coldly. Although feeling touched over Kisame's protectiveness. Kisame shrugged. "That's fine." He stated. Kakashi and Guy shared glances, unsure on what was happening.

"Then I would have come here dressed like this for no reason Kisame." Itachi's voice came out annoyed.

"Still not bothered." Kisame lifted Samehada."

"Then I would have fucked that ugly old man for nothing! Kisame don't make this more than it is." Itachi stated quickly and Kisame stilled. Sasuke reached for a blade, eyes on Itachi who glanced at him, face unreadable. Kisame growled, lowering his weapon.

"You're lucky I listen to him. I would sleep with one eye open if I were you." He turned on his heel and passed by Sasuke, shoving him aside and away from Itachi who took off for the door. Naruto stood where Sasuke had left him staring wide eyed.

"Take my advice brat," Kisame called out to him as he rushed by. "If you ever join any terrorist organization don't be labeled the pretty boy in the group! Otherwise you're going to end getting fucked by an old guy!"

"Kisame, watch your language!" Itachi shouted from the door, Guy taking off after him. Kisame followed close behind, with Jiraiya on his heels. This left Naruto, Sasuke and Kakashi in awkward silence. The bar had ceased movement, unsure on what had jut happened. Slowly, Sasuke turned to Kakashi who lifted his hands defensively, grinning slightly.

"In my defense, I didn't realize it was your brother." He pointed out, before rushing to join Guy and Jiraiya. Sasuke glared after the nin. Naruto shifting awkwardly. The benefactor shouted at the two boys.

"You tell that _friend_ of yours I'll get him for this!"

"Get in line!" Sasuke snarled at the man before taking off towards the door, Naruto at his heels.

Outside, Kisame and Guy were facing off. Jiraiya and Kashi stood watching, Itachi was no where in sight. Sasuke raced towards the pair.

"Where the fuck is he!?"The boy shouted, looking around wildly for his brother. Kisame and Guy ignored him, continuing their battle. Kakashi shook his head.

"Kisame." A familiar voice called out from the treeline. The battle stopped and everyone turned towards Itachi who was leaning against one of the trees looking bored. A large cloak was covering most of him, expect for some leg and bare feet peeking through. "The mission is over. Stop wasting time." Sasuke went to move towards Itachi but the teen shot him a glare. Sasuke scowled, Kakashi reaching forward, dragged the boy back.

"But Itachi-San- Kisame began only for that glare to land on him. Kisame stepped back sullenly."Okay..."

Itachi turned to Kakashi and glared.

"I'm quite positive that bringing children to a brothel is not exactly smiled upon Kakashi-San." Kisame fought down a snicker while Sasuke glared at the other Uchiha for speaking. Kakashi shrugged.

"Obviously it was worth it." He replied and Itachi tilted his head, fighting down a smile.

"Hn." Itachi turned on his heel, vanishing into the trees while Kisame shot a glare back at Guy. With the two missing nin gone, Jiraiya turned to Kakashi.

"You expect that?"

"Nope."

"Itachi has nice legs." The pervert noted and Kakashi nodded in agreement.

"Hey!' Sasuke snapped in annoyance and embarrassment.

"Kisses good too." Kakashi noted.

"HEY!"


End file.
